Enantioselectivity of alcohol-treated Candida rugosa lipase in the kinetic resolution of racemic methyl 2-aryloxypropionates in water and aqueous organic media

被引：18
|
作者：
Cipiciani, A [1 ]
Bellezza, F [1 ]
Fringuelli, F [1 ]
Stillitano, M [1 ]
机构：
[1] Univ Perugia, Dipartimento Chim, I-06100 Perugia, Italy
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 23期
关键词：
D O I：
10.1016/S0957-4166(99)00500-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Racemic methyl 2-aryloxypropionates (+/-)-1 were subjected to hydrolysis in water and in a series of two-phase aqueous organic media in the presence of Candida rugosa lipase (CRL). The biocatalytic material used was the enzyme of commercial CRL purified by treatment with different alcohols. The purification of CRL and the reaction medium play an important role in the enantioselection of racemates (+/-)-1 While it is not possible to use the same protocol for all substrates, by combining the different ways of purifying the enzyme with the various reaction media, it is possible to achieve high enantioselectivities of racemic esters. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4599 / 4605
页数：7
相关论文
共 13 条
  • [1] Improving the enantioselectivity of Candida rugosa lipase in the kinetic resolution of racemic methyl 2-(2,4-dichlorophenoxy)propionate
    Cipiciani, A
    Cittadini, M
    Fringuelli, F
    TETRAHEDRON, 1998, 54 (27) : 7883 - 7890
  • [2] Resolution of racemic acids, esters and amines by Candida rugosa lipase in slightly hydrated organic media
    Alcántara, AR
    de María, PD
    Fernández, M
    Hernaíz, MJ
    Sánchez-Montero, JM
    Sinisterra, JV
    FOOD TECHNOLOGY AND BIOTECHNOLOGY, 2004, 42 (04) : 343 - 354
  • [3] Effect of organic solvent type on the enantioselectivity of Candida rugosa lipase in the hydrolysis of racemic Naproxen methyl ester in biphasic reaction system
    Takaç, S
    Mutlu, D
    JOURNAL OF BIOTECHNOLOGY, 2005, 118 : S132 - S132
  • [4] Effect of pH in the 2-propanol treatment of Candida rugosa lipase on its enantioselectivity in the hydrolysis of racemic Naproxen methyl ester
    Takaç, S
    Ünlü, AE
    JOURNAL OF BIOTECHNOLOGY, 2005, 118 : S112 - S113
  • [5] Influence of pH and temperature on the enantioselectivity of propan-2-ol-treated Candida rugosa lipase in the kinetic resolution of (±)-4-acetoxy-[2,2]-paracyclophane
    Cipiciani, A
    Bellezza, F
    Fringuelli, F
    Silvestrini, MG
    TETRAHEDRON-ASYMMETRY, 2001, 12 (16) : 2277 - 2281
  • [6] The Candida antarctica lipase B catalysed kinetic resolution of seudenol in non-aqueous media of controlled water activity
    Orrenius, C.
    Norin, T.
    Hult, K.
    Carrea, G.
    Tetrahedron: Asymmetry, 6 (12):
  • [7] The Candida antarctica lipase B catalysed kinetic resolution of seudenol in non-aqueous media of controlled water activity
    Orrenius, C
    Norin, T
    Hult, K
    Carrea, G
    TETRAHEDRON-ASYMMETRY, 1995, 6 (12) : 3023 - 3030
  • [8] ESTERIFICATION OF 2-METHYLALKANOIC ACIDS CATALYZED BY LIPASE FROM CANDIDA-RUGOSA - ENANTIOSELECTIVITY AS A FUNCTION OF WATER ACTIVITY AND ALCOHOL CHAIN-LENGTH
    BERGLUND, P
    VORDE, C
    HOGBERG, HE
    BIOCATALYSIS, 1994, 9 (1-4): : 123 - 130
  • [9] Reactivity of pure Candida rugosa lipase isoenzymes (Lip1, Lip2, and Lip3) in aqueous and organic media.: Influence of the isoenzymatic profile on the lipase performance in organic media
    López, N
    Pernas, MA
    Pastrana, LM
    Sánchez, A
    Valero, F
    Rúa, ML
    BIOTECHNOLOGY PROGRESS, 2004, 20 (01) : 65 - 73
  • [10] Effect of acyl chain length and branching on the enantioselectivity of Candida rugosa lipase in the kinetic resolution of 4-(2-difluoromethoxyphenyl)-substituted 1,4-dihydropyridine 3,5-diesters
    Sobolev, A
    Franssen, MCR
    Vigante, B
    Cekavicus, B
    Zhalubovskis, R
    Kooijman, H
    Spek, AL
    Duburs, G
    de Groot, A
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02): : 401 - 410
12